Triphenylphosphine → 7-(Pyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[2,3-d]pyridazin-4(5H)-one

HRID 920903Notes

Reaction equation

HRID 920903 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]3[S:16][CH:15]=[CH:14][C:9]=3[C:10](=[O:13])[NH:11][N:12]=2)=[CH:3][CH:2]=1.[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[CH2:27][CH2:28]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:8]3[S:16][CH:15]=[CH:14][C:9]=3[C:10](=[O:13])[N:11]([CH2:28][CH2:27][C:18]3[CH:19]=[CH:20][C:21]4[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:17]=3)[N:12]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5462977Diethyl azodicarboxylateHCID 866831187-(pyridin-4-yl)thieno[3,2-d]pyridazin-4(5H)-one

Product 1

HCID 715574477-(Pyridin-4-yl)-5-[2-(quinolin-2-yl)ethyl]thieno[2,3-d]pyridazin-4(5H)-oneYield 11.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(pyridin-4-yl)thieno[3,2-d]pyridazin-4(5H)-one (100 mg, 0.44 mmol) from example 2.3, 2-quinolin-2-yl-ethanol from example a1 (83 mg, 0.48 mmol) and PPh3 (343 mg, 1.31 mmol) in DCM (10 mL), DEAD (228 mg, 1.31 mmol) was added dropwise. The mixture stirred at room temperature for 3 h, concentrated and the purified by Prep-HPLC to give the title compound as a white solid (20 mg, 11.8% yield).

Workup

  1. concentrationconcentrated
  2. customthe purified by Prep-HPLC

Sources & evidence

ORD record
ord-c7921e9f87814867b47e2b0cd1163bce
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

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